Water → HCID 637356, compound

HRID 231610Notes

Reaction equation

HRID 231610 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[CH2:12](Br)[CH:13]=[CH2:14].C([O-])([O-])=O.[K+].[K+].O>CC(C)=O>[CH2:14]([O:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:1]([CH3:4])([CH3:2])[CH3:3])[CH:13]=[CH2:12]

Participants

6

Reactant 4

HCID 962WaterHCID 69232-Tert-ButylphenolHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 637356HCID 637356, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of o-(t-butyl)-phenol (11.3 g; 75 mmol) in acetone (150 ml) is added allyl bromide (10.9 g, 1.2 equiv.) and anhydrous K2CO3. After stirring 18 hr at reflux, the reaction is added to water (200 ml) and extracted with 3×150 ml portions of petroleum ether. The combined organic layers are dried (MgSO4), filtered, and concentrated in vacuo to give the crude product, which is purified by silica gel (sg) chromatography (hexane elution) to yield 1-prop-2-enyloxy-2-t-butylbenzene (11.6 g; 81% yield).

Workup

  1. temperatureat reflux
  2. extractionextracted with 3×150 ml portions of petroleum ether
  3. dry with materialThe combined organic layers are dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give the crude product, which
  7. customis purified by silica gel (sg) chromatography (hexane elution)

Sources & evidence

ORD record
ord-b70be55eb3f548d0953a5da6841ae961
Source dataset
uspto-grants-1989_07
Patent number
US04847303

Reaction notes

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